HCID 87773595, compound → HCID 178431058, compound

HRID 1490795Notes

Reaction equation

HRID 1490795 reaction equation
O=C(NCCCc1ccccc1Cl)C(F)(F)F>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CCCC[N+](CCCC)(CCCC)CCCC.C[OH2+].C[OH2+].Cc1ccc(-c2ccc(CS(=O)(=O)[O-])cn2)nc1.[Ir].[Ir]>CC1(C)OB(c2ccc(CCCNC(=O)C(F)(F)F)c(Cl)c2)OC1(C)C.CC1(C)OB(c2ccc(Cl)c(CCCNC(=O)C(F)(F)F)c2)OC1(C)C

Participants

7

Reactant 1

HCID 87773595HCID 87773595, compound

Product 2

HCID 178431040HCID 178431040, compoundYield 10%HCID 178431058HCID 178431058, compoundYield 80%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 165587889Tetrabutylazanium {5'-methyl-[2,2'-bipyridin]-5-yl}methanesulfonateReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Following general procedure F using N‐(3‐(2‐chlorophenyl)propyl)‐2,2,2‐trifluoroacetamide (66.4 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and 1a (3.8 mg, 0.0075 mmol) in THF (1.25 mL). The reaction was stirred at 50 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 10:78:10 dimeta:meta:para borylation in 98% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1‐9:1) to give the title compound (as a 7:78:10 mixture of dimeta:meta:para ratio, as determined by 1 H NMR) as a colourless oil (97.1 mg, 0.24 mmol, 97%*).

Sources & evidence

ORD record
ord-3ec2ee240af144dd861e93268b4b0b1c
Source dataset
Borylation dataset from Roche

Reaction notes

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